What’s is the Best Caribbean Regatta?
Will you be Racing, Partying, or both at the Greatest Regatta Circuit of them all…
What’s Your Favourite Caribbean Regatta?
Discovering Your Best Caribbean Regatta. We all have different priorities, all the destinations come with the enticing prospect of weaving together the thrill of competitive sailing with the vibrant cultures and idyllic settings of the islands. The Caribbean regatta circuit offers a captivating tapestry of world-class yacht races to realxed races with a greater focus on the drinking and enterainment.
For those drawn to this unique confluence of sport and sophisticated leisure, navigating the extensive Caribbean Regatta Season to select an event that truly resonates is a journey of discernment. This guide provides a curated perspective on the premier sailing events, offering insights to help you pinpoint the best Caribbean regatta experience to match your aspirations.
Participation in Caribbean Reaggta. It is often much more accessible than one might imagine, with various avenues for engagement. A private yacht charter, whether for a fully crewed racing campaign or a more independent entry in the bareboat class, provides a direct immersion in the on-water action. Furthermore, cabin charters and individual race berths are frequently available for those wishing to join established teams for specific Caribbean regattas. While experienced sailors are always in demand, individuals newer to sailing or yacht racing will find many regattas offer a genuinely welcoming atmosphere and accessible pathways into this remarkable world. SailChecker is, of course, adept at facilitating such yacht charter arrangements, ensuring a seamless transition to your chosen Best Caribbean Regatta.
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How Do I Find Out More About A Caribbean Regatta?
SailChecker.com is a specialist yacht charter comparison site that deals with everything from individual berths to whole regattas, so why not get in contact with us.
Regattas are a great way to learn more about sailing and party at the after race balls. In fact, some will go along for the ride and not race at all!
Who Are Caribbean Regattas Aimed At?
Okay, so some make it their passion, and winning is everything. Some get themselves and or their yachts to the vicinity of a good regatta to feed the great atmosphere created, and there is a whole load of first-timers, singles, groups of friends, work colleagues, and families, to name but a few.
Your Guide to Caribbean Regattas: FAQs
Everything you need to know to choose the perfect sailing event in the Caribbean.
The peak Caribbean regatta season generally runs from late November/December through early May. This period offers the most favorable weather, consistent trade winds, and hosts the majority of the major international events.
The “best” regatta is subjective and depends on your preferences! Consider factors like the level of competition (from fun local races to world-class professional events), the type of boat you want to sail, the social atmosphere (party-focused vs. more laid-back), your budget, and the specific island destinations that appeal to you.
Events like the RORC Caribbean 600, Les Voiles de St. Barths, St. Thomas International Regatta (STIR), and Antigua Sailing Week attract top international racing teams and feature high-performance yachts.
Absolutely! Many regattas have “cruising” or “bareboat” classes with a more relaxed atmosphere. Events like the BVI Spring Regatta & Sailing Festival, Grenada Sailing Week, and some local island regattas are known for being very welcoming to less experienced racers and families.
The St. Maarten Heineken Regatta (“Serious Fun!”) is legendary for its nightly concerts. Antigua Sailing Week also has a very vibrant party scene. Many smaller regattas feature lively local festivities.
There are many options! You can book an individual berth on a race charter yacht, charter a bareboat (if qualified) and enter, or join a crew through crew-finder services. SailChecker specializes in helping individuals and groups find these opportunities.
Yes! The Caribbean hosts world-class specialized events such as the Antigua Classic Yacht Regatta, the Caribbean Multihull Challenge (St. Maarten), and superyacht regattas like the St. Barths Bucket and the Superyacht Challenge Antigua.
Costs can vary widely based on the event’s prestige, duration, boat type (charter vs. own boat), crew expenses, entry fees, berthing, travel, and shoreside spending. It’s best to research specific events and charter options.
Caribbean Regatta Quick Index
| Month | Regatta Name | Primary Location(s) | Navigate to Section |
|---|---|---|---|
| January | Barbados Sailing Week | Barbados | Go to January Events |
| Pineapple Cup Race | USA (Florida) to Jamaica | Go to January Events | |
| Grenada Sailing Week | Grenada | Go to January Events | |
| RORC Transatlantic Race (Finish) | Grenada | Go to January Events | |
| February | RORC Caribbean 600 | Antigua | Go to February Events |
| Caribbean Multihull Challenge | St. Maarten | Go to February Events | |
| Jolly Harbour Valentine’s Regatta | Antigua | Go to February Events | |
| Antigua 360 RTI Race | Antigua | Go to February Events | |
| Governors Cup (BVI) | BVI | Go to February Events | |
| March | St. Maarten Heineken Regatta | St. Maarten | Go to March Events |
| Superyacht Challenge Antigua | Antigua | Go to March Events | |
| Catamaran Regatta (High Point Yacht Fest BVI) | BVI | Go to March Events | |
| St. Barths Bucket Regatta | St. Barths | Go to March Events | |
| STIR Round St. John’s Race | St. Thomas, USVI | Go to March Events | |
| St. Thomas International Regatta (STIR) | St. Thomas, USVI | Go to March Events | |
| BVI Spring Regatta & Sailing Festival | BVI | Go to March Events | |
| April | Antigua Sailing Week | Antigua | Go to April Events |
| Les Voiles de St. Barths Richard Mille | St. Barths | Go to April Events | |
| Antigua Classic Yacht Regatta | Antigua | Go to April Events | |
| St. Croix International Regatta | St. Croix, USVI | Go to April Events | |
| Round Antigua Race | Antigua | Go to April Events | |
| May | Antigua Bermuda Race (Start) | Antigua (to Bermuda) | Go to May Events |
| BVI Dinghy Championships | BVI | Go to May Events | |
| STYC Invitational Regatta | St. Thomas, USVI | Go to May Events | |
| WindWard 500 Race Series (Grenada) | Grenada | Go to May Events | |
| October | Willy T Virgin’s Cup | BVI | Go to October Events |
| Helly Hansen Sailing World Regatta Series – Caribbean Champs. | BVI | Go to October Events | |
| The Moorings Interline Regatta | BVI | Go to October Events | |
| Harbour Island Regatta | Bahamas | Go to October Events | |
| November | St. Barth Cata-Cup | St. Barths | Go to November Events |
| Jolly Harbour Yacht Club Annual Regatta | Antigua | Go to November Events | |
| Mango Bowl Regatta | St. Lucia | Go to November Events | |
| Nanny Cay Round Tortola Race / Peg Legs Race Day | BVI | Go to November Events | |
| December | Nelson’s Pursuit Race | Antigua | Go to December Events |
| ARC (Atlantic Rally for Cruisers) Finish | St. Lucia | Go to December Events | |
| Carriacou Parang & Sailing Weekend | Carriacou, Grenada | Go to December Events | |
| Budget Marine High Tide Series (St. Maarten) | St. Maarten | Go to December Events |
Caribbean Regatta Quick Links
Caribbean Regattas and Some Famous Others Too
Caribbean Regattas in January
Caribbean Regattas in January 2026: Sun, Wind, and Competitive Spirit!
January 2026 is shaping up to be an incredible month to kick off your sailing year in the Caribbean! Expect fantastic trade winds, warm turquoise waters, and a vibrant atmosphere as the international racing calendar gets underway. Here are the premier regattas lighting up the Caribbean in January 2026:
Barbados Sailing Week
Location: Barbados (Events based around Carlisle Bay and the south/west coasts)
Dates: January 15th – 22nd, 2026
Organised by: Barbados Cruising Club, Barbados Tourism Marketing Inc. & Mount Gay Rum
A highlight of the early Caribbean racing season, Barbados Sailing Week attracts sailors worldwide. It’s famed for the iconic Mount Gay Round Barbados Race (scheduled around January 21st, 2026), where yachts compete not just for glory but also to break speed records. The week typically includes several days of exciting coastal racing, alongside a vibrant social scene deeply intertwined with Bajan culture and the island’s rich rum heritage. It’s an ideal event for charterers looking to experience top-class sailing alongside lively island festivities. The week often concludes with the “Rum to Spice Race” on January 22nd, leading yachts towards Grenada.
Highlights: Mount Gay Round Barbados Race, competitive coastal series, strong international fleet, legendary Mount Gay Rum parties, beautiful sailing conditions.
Grenada Sailing Week
Location: Grenada (Events often start in Carriacou and move to Port Louis Marina, St George’s)
Dates: January 25th – 30th, 2026
Organised by: Grenada Sailing Week Committee
Renowned for its excellent sailing conditions with consistent trade winds, Grenada Sailing Week offers challenging and scenic courses around Grenada and its sister isle, Carriacou. The 2026 event will welcome participants with festivities in Carriacou, including those arriving from the “Rum to Spice Race,” before transitioning to Grenada for several days of competitive racing. Known for a famously friendly and welcoming atmosphere, it attracts a mix of international racing yachts and strong local participation. Ideal for charterers and race teams looking for competitive yet relaxed regatta experiences in the southern Caribbean, complemented by fun social events showcasing Grenadian hospitality.
Highlights: Racing around Carriacou and Grenada, consistent trade winds, friendly international competition, vibrant shoreside events, “Spice Island” culture.
Caribbean Regattas in February
RORC Caribbean 600
Location: Antigua Yacht Club, Falmouth Harbour, Antigua
Dates: Starts Monday, February 23rd, 2026 (Race duration is several days)
Organised by: Royal Ocean Racing Club (RORC)
Coordinates: 17.008, -61.781
The RORC Caribbean 600 is a renowned and demanding offshore race, starting and finishing in Antigua. It takes competitors on a spectacular 600-nautical-mile journey around 11 Caribbean islands, attracting some of the world’s most competitive racing yachts and professional crews seeking a challenging start to their Caribbean racing season.
Highlights: Grueling 600nm course, circumnavigation of 11 Caribbean islands, attracts top international racing yachts (Maxis, Superyachts, etc.), stunning scenery and varied conditions.
Visit the official RORC Caribbean 600 site
Jolly Harbour Valentine’s Regatta
Location: Jolly Harbour Yacht Club, Antigua
Dates: Expected around February 13th – 15th, 2026 (Please check the official Jolly Harbour Yacht Club website for confirmation closer to the event)
Organised by: Jolly Harbour Yacht Club (JHYC)
Coordinates: 17.082, -61.892
The Jolly Harbour Valentine’s Regatta is a popular and friendly event held in the picturesque setting of Jolly Harbour, Antigua. Known for its fun atmosphere and competitive spirit, it attracts a mix of local boats, cruising yachts, and international visitors for several days of racing and enjoyable shoreside activities, often with a festive Valentine’s theme.
Highlights: Fun Valentine’s theme, competitive racing for various classes, relaxed and social atmosphere, beautiful Jolly Harbour location.
Visit the official Jolly Harbour Yacht Club site
Antigua 360 RTI Race
Location: Antigua Yacht Club, Falmouth Harbour, Antigua
Dates: Dates vary, often held in February (Please check the official Antigua Yacht Club website for scheduling, as this race can be a standalone event or linked with other regattas like the RORC Nelson’s Cup Series)
Organised by: Antigua Yacht Club (AYC)
Coordinates: 17.008, -61.781
The Antigua 360 Round The Island (RTI) Race is an exciting event that challenges sailors to circumnavigate the island of Antigua. Covering approximately 50 nautical miles, the race offers tactical challenges with varied conditions and stunning coastal views, providing a true test of seamanship and a great day of racing.
Highlights: Full circumnavigation of Antigua, scenic coastal course, tactical racing, often attracts a diverse fleet.
Visit the official Antigua Yacht Club site
Caribbean Multihull Challenge
Location: Simpson Bay, St. Maarten
Dates: January 28th – February 1st, 2026
Organised by: St. Maarten Yacht Club (SMYC)
Coordinates: 18.035, -63.103
The Caribbean Multihull Challenge, hosted by the St. Maarten Yacht Club, is a premier event dedicated entirely to multihull sailing. It offers several days of exciting racing action tailored for a diverse fleet of catamarans and trimarans, from high-performance racers to comfortable cruisers, all vying for honors in the beautiful waters around St. Maarten.
Highlights: Exclusively for multihulls, varied racing formats, strong international participation, vibrant St. Maarten sailing scene.
Visit the official Caribbean Multihull Challenge site
Governors Cup (BVI)
Location: Royal BVI Yacht Club, Road Town, Tortola, BVI
Dates: Dates vary (Please check the official Royal BVI Yacht Club website for scheduling, as this may be part of a series, a specific club event, or linked to other major regattas in the BVI)
Organised by: Royal BVI Yacht Club (RBVIYC)
Coordinates: 18.424, -64.615
The Governors Cup is a notable local regatta hosted by the Royal BVI Yacht Club in the stunning sailing paradise of the British Virgin Islands. While specifics can vary year to year, it typically features competitive racing for various classes, drawing on the strong local sailing talent and visiting yachts to celebrate sailing in the BVI.
Highlights: Prestigious local BVI event, competitive racing in ideal conditions, hosted by the Royal BVI Yacht Club.
Visit the official Royal BVI Yacht Club site
Caribbean Regattas in March
St. Maarten Heineken Regatta
Location: Simpson Bay, St. Maarten (operations often from St. Maarten Yacht Club)
Dates: March 5 – 8, 2026
Organised by: St. Maarten Yacht Club
Coordinates: 18.035, -63.103
The St. Maarten Heineken Regatta is one of the largest and most popular annual regattas in the Caribbean, famous for its “Serious Fun!” motto. It attracts a massive international fleet of racing and cruising yachts for four days of competitive sailing around St. Maarten/St. Martin, combined with legendary nightly concerts and parties featuring international artists.
Highlights: “Serious Fun!” atmosphere, large international fleet (200+ boats), diverse classes, around-the-island race, major nightly concerts, strong global participation.
Visit the official St. Maarten Heineken Regatta site
Superyacht Challenge Antigua
Location: Nelson’s Dockyard / Antigua Yacht Club, English Harbour, Antigua
Dates: March 11 – 16, 2026
Organised by: Superyacht Challenge Antigua Committee & Antigua Yacht Club
Coordinates: 17.008, -61.781
The Superyacht Challenge Antigua is an exclusive invitational event designed for sailing superyachts of 80ft and over. It focuses on fair, fun, and competitive racing with an emphasis on sportsmanship, held in the stunning sailing waters off Antigua’s south coast. The event is known for its friendly atmosphere among owners, guests, and crew.
Highlights: Exclusively for superyachts (80ft+), gentlemanly racing rules, spectacular fleet, beautiful Antiguan sailing conditions, exclusive social events.
Visit the official Superyacht Challenge Antigua site
Catamaran Regatta (High Point Yacht Fest BVI)
Location: British Virgin Islands (specific locations may vary, often utilizing areas like Nanny Cay or Scrub Island)
Dates: Dates for a March 2026 event are not yet confirmed. Please check the official High Point Yacht Fest website for updates. (Previous events have been held in different months).
Organised by: High Point Yachting
Coordinates: 18.397, -64.630 (Nanny Cay, a common BVI regatta hub)
The High Point Yacht Fest aims to offer unique sailing experiences in the BVI, including a “Catamaran Fun Regatta” as part of its festivities. These events focus on enjoyable sailing, camaraderie, and exploring the beauty of the islands, often combining relaxed racing with social gatherings and themed parties.
Highlights: Focus on catamaran sailing, fun regatta atmosphere, BVI island exploration, social events. (Event details and specific focus may vary, check official site for latest info).
Visit the official High Point Yacht Fest site
St. Barths Bucket Regatta
Location: Gustavia Harbour, St. Barthélemy
Dates: March 19 – 22, 2026
Organised by: Bucket Regattas LLC
Coordinates: 17.897, -62.851
The St. Barths Bucket is a prestigious invitational regatta for large sailing superyachts (typically over 100ft LOA). It’s renowned for its spirit of camaraderie and non-commercial, fun-focused racing around the stunning island of St. Barthélemy. The event is a spectacular display of the world’s most impressive sailing yachts.
Highlights: Elite fleet of large superyachts, emphasis on fun and safe racing, spectacular scenery of St. Barths, exclusive and elegant shoreside atmosphere.
Visit the official St. Barths Bucket Regatta site
STIR Round St. John Race
Location: St. Thomas Yacht Club, Cowpet Bay, St. Thomas, USVI (Race circumnavigates St. John)
Dates: Typically held just before or on the first day of the St. Thomas International Regatta (e.g., around March 26th or 27th, 2026, please confirm with STIR schedule).
Organised by: St. Thomas Yacht Club
Coordinates: 18.315, -64.848 (St. Thomas Yacht Club)
The Round St. John Race is often a challenging and scenic precursor or component of the St. Thomas International Regatta (STIR). It takes competitors on a course around the beautiful island of St. John, USVI, offering varied conditions and stunning views, serving as an excellent warm-up or standalone achievement.
Highlights: Scenic course around St. John, tactical challenges, often part of the larger STIR event, showcases the beauty of the US Virgin Islands.
Visit the official St. Thomas International Regatta site for details
St. Thomas International Regatta (STIR)
Location: St. Thomas Yacht Club, Cowpet Bay, St. Thomas, USVI
Dates: March 27 – 29, 2026
Organised by: St. Thomas Yacht Club
Coordinates: 18.315, -64.848
The St. Thomas International Regatta (STIR) is known as the “Crown Jewel of Caribbean Racing.” It offers three days of professionally managed, highly competitive racing for a wide range of classes, including CSA racing boats, IC24s, and often cruising classes. The event is famed for its reliable winds, challenging courses, and warm island hospitality.
Highlights: “Crown Jewel of Caribbean Racing,” highly competitive, multiple classes including one-designs, professional race management, beautiful USVI sailing conditions, fun social events.
Visit the official St. Thomas International Regatta site
BVI Spring Regatta & Sailing Festival
Location: Nanny Cay Resort & Marina, Tortola, British Virgin Islands (Festival may include races to other BVI islands)
Dates: March 30 – April 5, 2026 (Sailing Festival typically March 30-31, main Regatta April 1-5)
Organised by: Royal BVI Yacht Club
Coordinates: 18.397, -64.630 (Nanny Cay)
The BVI Spring Regatta & Sailing Festival is a week-long celebration of sailing in the beautiful British Virgin Islands. The event kicks off with a Sailing Festival featuring warm-up races and cruising to different BVI locations, followed by three days of world-class racing in the main Spring Regatta. It attracts a diverse international fleet and is known for its friendly atmosphere and stunning racecourses around the islands.
Highlights: Week-long event (Festival + Regatta), diverse fleet (racers, cruisers, bareboats), beautiful BVI courses around multiple islands, strong shoreside party scene, “Warm Water, Hot Racing.”
Visit the official BVI Spring Regatta & Sailing Festival site
Caribbean Regattas in April
Antigua Sailing Week
Location: Nelson’s Dockyard, English Harbour & Falmouth Harbour, Antigua
Dates: April 25th – May 1st, 2026 (Starts in April, concludes in May)
Organised by: Antigua Sailing Week Committee
Coordinates: 17.0085, -61.7645
Antigua Sailing Week is one of the world’s premier and longest-established sailing regattas, attracting a large international fleet of racing and cruising yachts. It features professionally managed racing around Antigua’s stunning south coast, coupled with vibrant daily prize-givings and legendary shoreside parties, culminating in a grand final awards ceremony.
Highlights: Major international regatta, diverse fleet (Maxis, racers, cruisers, bareboats), “Round Antigua Race” often precedes, Lay Day beach party, exceptional organization and racing.
Visit the official Antigua Sailing Week site
Les Voiles de St. Barths Richard Mille
Location: Gustavia Harbour, St. Barthélemy
Dates: April 13 – 19, 2026
Organised by: An independent organizing committee with the support of the St. Barths Yacht Club.
Coordinates: 17.897, -62.851
Les Voiles de St. Barths Richard Mille has quickly become a key event in the Caribbean calendar, attracting a fleet of very modern, high-performance racing yachts (Maxis, TP52s, etc.) as well as classic yachts. It’s renowned for its chic French Caribbean atmosphere, challenging courses designed by professional racers, and high-end competitive sailing combined with elegant social events.
Highlights: High-performance racing fleet, classic yachts, chic St. Barths atmosphere, challenging courses, top-tier international sailors.
Visit the official Les Voiles de St. Barths Richard Mille site
Antigua Classic Yacht Regatta
Location: Antigua Yacht Club / Nelson’s Dockyard, Falmouth Harbour, Antigua
Dates: April 16 – 22, 2026
Organised by: Antigua Classic Yacht Regatta Committee
Coordinates: 17.008, -61.781
The Antigua Classic Yacht Regatta is a world-renowned celebration of classic and vintage yachts. It features several days of spectacular racing with a fleet of stunning traditional vessels, Carriacou sloops, and Spirit of Tradition yachts. The event emphasizes seamanship, camaraderie, and the beauty of these historic boats, with a vibrant social program.
Highlights: World-class fleet of classic and vintage yachts, traditional sailing, Parade of Classics, Concours d’Elégance, unique community spirit.
Visit the official Antigua Classic Yacht Regatta site
St. Croix International Regatta
Location: St. Croix Yacht Club, Teague Bay, St. Croix, USVI
Dates: Typically held in April (2026 dates TBC, please check the official St. Croix Yacht Club website for confirmation closer to the event)
Organised by: St. Croix Yacht Club (SCYC)
Coordinates: 17.755, -64.600
The St. Croix International Regatta is a well-established event known for its friendly island hospitality and competitive racing in the beautiful waters off St. Croix. It typically attracts a diverse fleet from across the Caribbean, including racing monohulls, multihulls, and often one-design classes, enjoying the challenging conditions and social gatherings hosted by the St. Croix Yacht Club.
Highlights: Friendly “Race in Paradise” atmosphere, varied fleet, good conditions in Teague Bay, strong local and regional participation.
Visit the St. Croix Yacht Club Regattas page
Round Antigua Race (Peters & May or other sponsor)
Location: Starts and finishes off Falmouth Harbour, Antigua
Dates: Typically the Saturday before Antigua Sailing Week (e.g., April 25th, 2026, if ASW starts on this Saturday. Confirm with ASW schedule)
Organised by: Antigua Sailing Week Committee / Antigua Yacht Club
Coordinates: 17.008, -61.781 (Falmouth Harbour)
The Round Antigua Race serves as an exciting precursor to the main Antigua Sailing Week events. This challenging day race takes competitors on a full circumnavigation of the island of Antigua, covering approximately 52 nautical miles. It’s a great test of strategy and endurance, often attracting many of the yachts participating in the subsequent week of racing.
Highlights: Full island circumnavigation, standalone race often opening Antigua Sailing Week festivities, tactical challenges, attracts a large and diverse fleet.
Visit the official Antigua Sailing Week site for Race Details
Caribbean Regattas in May
Antigua Bermuda Race
Location: Starts from English Harbour/Falmouth Harbour, Antigua (Finishes in Bermuda)
Dates: Early May (Typically starts a few days after Antigua Sailing Week. For 2026, expect around May 3rd-6th. Please verify the exact start date on the official website.)
Organised by: Royal Bermuda Yacht Club in association with Antigua Sailing Week (often RORC endorsed)
Coordinates: 17.008, -61.781 (Antigua Start Point)
The Antigua Bermuda Race is a popular 935-nautical-mile offshore race connecting two iconic sailing destinations. Starting from Antigua after its main sailing season, the race provides a challenging passage north, requiring strategic navigation, often involving the Gulf Stream, as yachts head towards Bermuda.
Highlights: Significant offshore race (935nm), links Antigua and Bermuda, tactical navigation challenges, attracts a diverse fleet of offshore-capable yachts.
Visit the official Antigua Bermuda Race site
BVI Dinghy Championships
Location: Royal BVI Yacht Club, often based at Nanny Cay, Tortola, BVI
Dates: Typically mid-May (e.g., around May 16-17, 2026. Please check the official Royal BVI Yacht Club website for confirmed 2026 dates.)
Organised by: Royal BVI Yacht Club (RBVIYC)
Coordinates: 18.397, -64.630 (Nanny Cay, a common BVI regatta hub)
The BVI Dinghy Championships is a key event in the British Virgin Islands for youth and dinghy sailors. It showcases talent across various dinghy classes and provides a competitive yet supportive environment for skill development, hosted in the beautiful waters of the BVI.
Highlights: Premier BVI dinghy sailing event, focuses on youth development, multiple dinghy classes, competitive racing.
Visit the official Royal BVI Yacht Club site
STYC Invitational Regatta
Location: St. Thomas Yacht Club, Cowpet Bay, St. Thomas, USVI
Dates: Dates vary. St. Thomas Yacht Club hosts various invitational events throughout the year. Please check the official STYC sailing calendar for specific May events.
Organised by: St. Thomas Yacht Club (STYC)
Coordinates: 18.315, -64.848
The St. Thomas Yacht Club frequently hosts invitational regattas, welcoming various classes for competitive racing in the challenging and scenic waters around St. Thomas. These events often highlight the club’s strong racing programs and warm hospitality, offering great sailing for local and visiting crews.
Highlights: Club-hosted invitational racing, potential for various classes, beautiful St. Thomas sailing venue, local and visiting sailor participation. (Details specific to any given May invitational should be confirmed via STYC).
Visit the St. Thomas Yacht Club Regattas page
WindWard 500 Race Series (Grenada)
Location: Based in or incorporating Grenada (Specifics of route/base to be confirmed).
Dates: Information on a regularly scheduled “WindWard 500 Race Series” in May originating from Grenada is not widely available. If this is a specific or niche event, please verify details and dates with event organizers or local sailing associations in Grenada.
Organised by: To be confirmed based on event specifics.
Coordinates: 12.056, -61.750 (St. George’s, Grenada – general reference)
A “WindWard 500 Race Series” based in Grenada would likely offer challenging offshore or inter-island racing through the Windward Islands. Such an event would test navigational skills and endurance over a significant distance, showcasing the superb sailing conditions of the Southern Caribbean.
Highlights: Potential for long-distance offshore/inter-island racing, navigation through the Windward Islands, competitive sailing. (Details are highly dependent on the specific event existing and its format).
(Official website link to be added if a specific, recurring event is identified)
Caribbean Regattas in October
Willy T Virgin’s Cup
Location: British Virgin Islands (Hosted by Royal BVI Yacht Club)
Dates: Saturday, October 18, 2025
Organised by: Royal BVI Yacht Club (RBVIYC)
Coordinates: 18.397, -64.630 (Nanny Cay, common RBVIYC event area)
The Willy T Virgin’s Cup, launched in 1975, remains a vibrant and inclusive regatta in the Caribbean sailing calendar and a local favourite in the BVI. This event draws competitive sailors and social cruisers alike, known for its lively atmosphere and spirited racing. It is both a serious regatta and a fun celebration of Caribbean sailing culture, with a notable commitment to diversity and community participation, as seen in the 2024 edition where many boats were helmed by women.
Highlights: Long-standing local BVI regatta, inclusive atmosphere for racers and cruisers, promotes diversity in sailing, lively and spirited racing, celebration of Caribbean sailing culture.
Learn more from the Royal BVI Yacht Club
Caribbean Regattas in November
St. Barth Cata-Cup
Location: St. Jean Beach, St. Barthélemy
Dates: November 19 – 24, 2025 (Please verify exact 2025/2026 dates on the official website)
Organised by: St. Barth Multihull Association
Coordinates: 17.900, -62.841
The St. Barth Cata-Cup is a highly competitive and prestigious regatta dedicated to Formula 18 catamarans. Attracting top international F18 sailors, the event features intense racing in the stunning turquoise waters and challenging winds around St. Jean, combined with the island’s chic and welcoming atmosphere.
Highlights: Premier international F18 catamaran regatta, top-level sailors, challenging wind and sea conditions, beautiful St. Barths setting, high-energy racing.
Visit the official St. Barth Cata-Cup site
Jolly Harbour Yacht Club Annual Regatta
Location: Jolly Harbour Yacht Club, Antigua
Dates: Typically late November (e.g., around Nov 21-23, 2025. Please confirm specific dates with JHYC)
Organised by: Jolly Harbour Yacht Club (JHYC)
Coordinates: 17.082, -61.892
The Jolly Harbour Yacht Club’s Annual Regatta is a key event in their calendar, offering a friendly yet competitive environment for local and visiting sailors. The regatta usually features racing for various classes within the scenic waters around Jolly Harbour and Antigua’s west coast, complemented by social events at the club.
Highlights: Club-organized annual event, participation from local and visiting yachts, racing for multiple classes, social atmosphere at JHYC.
Visit the Jolly Harbour Yacht Club Events page
Mango Bowl Regatta
Location: St. Lucia Yacht Club, Rodney Bay, St. Lucia
Dates: Typically late November (e.g., around Nov 22-23, 2025. Please confirm specific dates with St. Lucia Yacht Club)
Organised by: St. Lucia Yacht Club
Coordinates: 14.076, -60.953
The Mango Bowl Regatta is one of St. Lucia’s premier sailing events, known for its competitive racing and lively shoreside ambiance. It attracts a strong fleet from St. Lucia and neighboring islands, competing in various classes in the beautiful setting of Rodney Bay. The event is a highlight of the southern Caribbean racing circuit.
Highlights: Major St. Lucian sailing event, competitive fleet from across the southern Caribbean, racing in Rodney Bay, fun social events.
Visit the St. Lucia Yacht Club site
Nanny Cay Round Tortola Race / Peg Legs Race Day
Location: Nanny Cay Resort & Marina, Tortola, BVI
Dates: Dates vary, often a race is held in November or as part of their Christmas series in December (e.g., “Peg Legs Race Day”). Please check the Nanny Cay or Royal BVI Yacht Club calendar for specific November 2025/2026 events.
Organised by: Nanny Cay Resort & Marina / Royal BVI Yacht Club
Coordinates: 18.397, -64.630
Nanny Cay often hosts exciting race days, including the challenging Round Tortola Race (sometimes known as the “Peg Legs Round Tortola Race”). These events showcase the stunning sailing around Tortola and are popular with local BVI sailors and visiting yachts, offering a great day of competitive racing and shoreside camaraderie at Nanny Cay.
Highlights: Scenic Round Tortola course, local BVI fleet participation, often hosted or supported by Nanny Cay Marina and RBVIYC.
Check Nanny Cay Sailing Events
Caribbean Regattas in December
Nelson’s Pursuit Race
Location: English Harbour / Falmouth Harbour, Antigua
Dates: December 31st annually
Organised by: Antigua Yacht Club & Nelson’s Dockyard
Coordinates: 17.008, -61.781 (Antigua Yacht Club area)
The Nelson’s Pursuit Race is a historic and unique event held annually on New Year’s Eve in Antigua. Based on Lord Nelson’s famous pursuit of the French fleet, yachts are given staggered start times according to their handicap, with the theoretical finish time being the same for all. It’s a fun and challenging race culminating in celebrations at Nelson’s Dockyard.
Highlights: Historic pursuit race format, New Year’s Eve tradition in Antigua, diverse fleet participation, finishes in scenic Nelson’s Dockyard.
Visit the Antigua Yacht Club site for details
ARC (Atlantic Rally for Cruisers) Finish
Location: Rodney Bay, St. Lucia
Dates: Fleet arrivals throughout December (Rally typically departs Las Palmas in late November)
Organised by: World Cruising Club
Coordinates: 14.076, -60.953
While not a regatta in the traditional racing sense, the arrival of the ARC fleet in St. Lucia throughout December is a major event in the Caribbean sailing calendar. Hundreds of yachts complete their transatlantic crossing, bringing a vibrant atmosphere to Rodney Bay with celebrations, prize-givings, and a strong sense of accomplishment among participants.
Highlights: Culmination of the world’s largest transatlantic rally, hundreds of participating yachts, vibrant international atmosphere in Rodney Bay, extensive social program and support for finishers.
Visit the official ARC (World Cruising Club) site
Carriacou Parang & Sailing Weekend
Location: Carriacou, Grenada (Events often in Windward and Hillsborough)
Dates: Typically early to mid-December (Please check local Grenada/Carriacou tourism sites for specific 2025/2026 dates)
Organised by: Local Carriacou committees & sailing community
Coordinates: 12.483, -61.457 (Hillsborough, Carriacou)
The Carriacou Parang & Sailing Weekend is a unique cultural event blending traditional workboat sailing with the vibrant sounds of Parang music. This festive weekend celebrates Carriacou’s rich boatbuilding and musical heritage, featuring exciting races between locally built sloops and gaff-rigged boats, alongside lively Parang performances and community gatherings.
Highlights: Traditional Caribbean workboat racing, celebration of Parang music and local culture, community-focused event, unique Carriacou heritage.
(Official website link to be added – often promoted via Grenada Tourism Authority or local Carriacou news)
Budget Marine High Tide Series (St. Maarten)
Location: Simpson Bay, St. Maarten
Dates: Series often includes races in December (Part of a multi-month series. Please check the St. Maarten Yacht Club calendar for specific December race dates).
Organised by: St. Maarten Yacht Club (SMYC)
Coordinates: 18.035, -63.103
The Budget Marine High Tide Series, hosted by the St. Maarten Yacht Club, offers competitive racing for local and visiting sailors across several months, often including race days in December. This series provides regular opportunities for keelboats to engage in well-organized racing in the waters around St. Maarten.
Highlights: Regular club racing series, participation from local St. Maarten fleet, competitive keelboat classes, hosted by SMYC.
Visit the St. Maarten Yacht Club Racing page
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